Journal of Chemical Crystallography

, Volume 36, Issue 11, pp 709–714 | Cite as

PM3 semiempirical study and its comparison with X-ray crystal structure of 4-[2-Methyl-4-(4-methoxyphenylazo)] phenoxyphtalonitrile

  • Nazan Ocak İskeleli
  • Hasan Karabıyık
  • Çiğdem Albayrak
  • Hande Petek
  • Erbil Ağar

The molecular and crystal structures of the title compound, C22H16N4O2, were determined by single crystal X-ray diffraction technique. The title compound crystallizes in monoclinic space group P1 2 1 /n1, with a=12.7811(9) Å, b=8.2002(4) Å, c=17.8772(14) Å, Z=4, D calc=1.3112(1) g/cm3, μ (Mo-Kα)=0.087 mm−1. The structure was solved by direct methods and refined to a final R=0.056 for 1891 reflections with I > 2σ (I). The asymmetric unit in the crystal structure contains only one neutral molecule. The positions of nitrogen atoms in the azo groups were disordered. There is no classic hydrogen bond in the crystal structure. The molecules in the crystal structure are stacked by π–π stacking and one edge-to-face interactions. In order to determine conformational flexibility and crystal packing effects on the molecules, molecular energy profile of the title compound was obtained with respect to the selected torsion angle, which is varied from −180° to +180° in every 10° via PM3 semi-empirical method.


azo compound phtalonitrile; PM3 crystal structure conformational analysis. 



Hasan Karabıyık would like to thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) for partial financial support. In addition, the authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the STOE IPDS II diffractometer (purchased under grants F.279 and F.377 of the University Research Fund).


  1. 1.
    Koh, J.; Greaves, A.J. Dyes Pigments 2001, 50, 117.CrossRefGoogle Scholar
  2. 2.
    Hallas, G.; Choi, J.H. Dyes Pigments 1999, 40, 119.CrossRefGoogle Scholar
  3. 3.
    Kandil, S.S. Trans. Met. Chem. 1998, 23, 461.CrossRefGoogle Scholar
  4. 4.
    Lee, M.-J.; Yoo, B.W.; Shin, S.T.; Keum, S.R. Dyes Pigments 2001, 51, 15.CrossRefGoogle Scholar
  5. 5.
    Aramaki, S.; Atkinson, G.H. J. Am. Chem. Soc. 1992, 114, 438.CrossRefGoogle Scholar
  6. 6.
    Tamai, N.; Miasaka, H. Chem. Rev. 2000, 100, 1875.CrossRefGoogle Scholar
  7. 7.
    Azuki, M.; Morihashi, K.; Watanabe, T.; Taskahashi, O.; Kikuchi, O. J. Mol. Struc.: THEOCHEM 2001, 542, 255.CrossRefGoogle Scholar
  8. 8.
    Grebenkin, S.Y.; Bolshakov, B.V. J. Photochem. Photobiol. A: Chem. 1999, 122, 205.CrossRefGoogle Scholar
  9. 9.
    Stoe & Cie, X-ARAEA (Version 1.18) and X-RED32 (Version 1.04), Darmstadt, Germany, 2002.Google Scholar
  10. 10.
    Sheldrick, G.M. SHELXS-97, Program for the solution of crystal structures, University of Göttingen, Germany, 1997.Google Scholar
  11. 11.
    Sheldrick, G.M. SHELXL-97, Program for crystal structure refinement, University of Göttingen, Germany, 1997.Google Scholar
  12. 12.
    Stewart, J.J.P. J. Comput. Chem. 1989, 10, 209.CrossRefGoogle Scholar
  13. 13.
    Stewart, J.J.P. J. Comput. Chem. 1989, 10, 221.CrossRefGoogle Scholar
  14. 14.
    Roothaan, C.C.J. Rev. Mod. Phys. 1951, 23, 69.CrossRefGoogle Scholar
  15. 15.
    Shchepin, R.; Litvinov, D. WinMopac Version 7.21, Semiempirical calculations program; Perm State University, Russia, 1998.Google Scholar
  16. 16.
    Farrugia, L.J. J. Appl. Cryst. 1997, 30, 565.CrossRefGoogle Scholar
  17. 17.
    Albayrak, Ç.; Odabaşoğlu, M.; Büyükgüngör, O.; Lönnecke, P. Acta Cryst. 2004, C 60, o318.Google Scholar
  18. 18.
    Şahin, O.; Albayrak, Ç.; Odabaşoğlu, M.; Büyükgüngör, O. Acta Cryst. 2005, E 61, o4149.Google Scholar
  19. 19.
    Şahin, O.; Albayrak, Ç.; Odabaşoğlu, M.; Büyükgüngör, O. Acta Cryst. 2005, E 61, o4154.Google Scholar
  20. 20.
    Adams, H.; Allen, R.W.K.; Chin, J.; O'Sullivan, B.; Styring, P.; Sutton, L.R. Acta Cryst. 2004, E 60, o289.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Nazan Ocak İskeleli
    • 1
  • Hasan Karabıyık
    • 2
    • 5
  • Çiğdem Albayrak
    • 3
  • Hande Petek
    • 4
  • Erbil Ağar
    • 3
  1. 1.Department of Science EducationOndokuz Mayıs UniversitySinopTurkey
  2. 2.Department of PhysicsDokuz Eylül Universityİzmir,Turkey
  3. 3.Department of ChemistryOndokuz Mayıs UniversitySamsun,Turkey
  4. 4.Department of PhysicsOndokuz Mayıs UniversitySamsunTurkey
  5. 5.To whom correspondence should be addressedSamsunTurkey

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